In the field of production of optically active amines, many asymmetric reactions including asymmetric reduction have been developed, and many asymmetric reactions using asymmetric metal complexes having optically active phosphine ligands have been reported. Meanwhile, there are many reports stating that complexes in which an optically active nitrogen compound is coordinated to a transition metal such as, for example, ruthenium, rhodium, or iridium have excellent performances as catalysts for asymmetric synthesis reactions (see Chem. Rev. (1992), p. 1051, J. Am. Chem. Soc. 117 (1995), p. 7562, J. Am. Chem. Soc. 118 (1996), p. 2521, and J. Am. Chem. Soc. 118 (1996), p. 4916). In particular, synthesis of optically active amines by hydrogenation reaction has been reported in recent years (see J. Am. Chem. Soc. 133 (2011), p. 9878, and Angew. Chem. Int. Ed 51 (2012), p. 5706).
However, conventional asymmetric synthesis methods using these complexes are insufficient in terms of catalytic activity or enantiomeric excess in some cases depending on the target reaction substrate. Hence, further development of such a complex has been desired.